Abstract
The carbonyl group is one of the most prevalent of the functional groups; great importance is therefore attached both to mechanistic studies and to reactions of the carbonyl group in organic synthesis. Most of the reactions of aldehydes, ketones, esters, amides, and other carboxylic acid derivatives are intimately associated with the carbonyl group. In Chapter 7, the role of the carbonyl group in stabilizing carbanion centers was discussed. The first two chapters of Part B deal heavily with the chemistry of carbonyl compounds, reflecting the importance of the carbonyl group in organic synthesis. In this chapter, the primary topic for discussion will be the characteristic mechanistic patterns of reactions at carbonyl centers.
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General References
R. P. Bell, Adv. Phys. Org. Chem. 4, 1 (1966).
T. C. Bruice and D. Piszkiewicz, J. Am. Chem. Soc. 89, 3568 (1967).
M. b. M. M. Kreevoy and R. W. Taft, Jr., J. Am. Chem. Soc. 77, 5590 (1955).
M. M. Kreevoy, C. R. Morgan, and R. W. Taft, Jr., J. Am. Chem. Soc. 82, 3064 (1960).
T. Maugh, II, and T. C. Bruice, J. Am. Chem. Soc. 93, 3237 (1971).
L. E. Eberson and L.-Ã…. Svensson, J. Am. Chem. Soc. 93, 3827 (1971).
A. Williams and G. Salvadori, J. Chem. Soc. Perkin Trans. 2, 883 (1972).
G. A. Rogers and T. C. Bruice, J. Am. Chem. Soc. 96, 2463 (1974).
K. Bowden and G. R. Taylor, J. Chem. Soc. B, 145, 149 (1971)
M. S. Newman and A. L. Leegwater, J. Am. Chem. Soc. 90, 4410 (1968).
T. C. Bruice and S. J. Benkovic, J. Am. Chem. Soc. 85, 1 (1963).
E. H. Cordes and W. P. Jencks. J. Am. Chem. Soc. 85, 2843, (1963).
E. Anderson and T. H. Fife, J. Am. Chem. Soc. 95, 6437 (1973).
M. W. Williams and G. T. Young, J. Chem. Soc., 3701 (1964).
R. Breslow and C. McAllister, J. Am. Chem. Soc. 93, 7096 (1971).
H. R. Mahler and E. H. Cordes, Biological Chemistry, Harper and Row, New York, 1966, p. 201.
R. P. Bell, M. H. Rand, and K. M. A. Wynne-Jones, Trans. Faraday Soc. 52, 1093 (1956).
J. Hine M. S. Cholod, and W. K. Chess, Jr., J. Am. Chem. Soc. 95, 4270 (1973).
H. G. Bull, K. Koehler, T. C. Pletcher, J. J. Ortiz, and E. H. Cordes, J. Am. Chem. Soc. 93, 3002 (1971).
J. A. Moore and D. L. Dalrymple, Experimental Methods in Organic Chemistry, W. B. Saunders Co., Philadelphia, 1971, p. 168.
J. F. Arens, Rec. Trav. Chim. Pays-Bas 74, 769 (1955).
R. Paul and G. W. Anderson, J. Am. Chem. Soc. 82, 4596 (1960).
D. S. Noyce and R. M. Pollack, J. Am. Chem. Soc. 91, 7158 (1969).
J. F. Kirsch and A. Kline, J. Am. Chem. Soc. 91, 1841 (1969).
D. N. Kevill and F. D. Foss, J. Am. Chem. Soc. 91, 5054 (1969).
L. doAmaral, M. P. Bastos, H. G. Bull, and E. H. Cordes, J. Am. Chem. Soc. 95, 7369 (1973).
T. C. Bruice and I. Oka, J. Am. Chem. Soc. 96, 4500 (1974).
R. Hershfield and G. L. Schmir, J. Am. Chem. Soc. 95, 7359 (1973).
T. H. Fife and J. E. C. Hutchins, J. Am. Chem. Soc. 94, 2837 (1972).
J. Hine, J. C. Craig, Jr., J. G. Underwood, II, and F. A. Via, J. Am. Chem. Soc. 92, 5194 (1970).
R. L. Schowen, C. R. Hopper, and C. M. Bazikian, J. Am. Chem. Soc. 94, 3095 (1972).
A. L. Mori and L. L. Schaleger, J. Am. Chem. Soc. 94, 5039 (1972).
E. H. Cordes and W. P. Jencks, J. Am. Chem. Soc. 85, 2843 (1963).
G. A. Rogers and T. C. Bruice, J. Am. Chem. Soc. 96, 2463 (1974).
T. S. Davies, P. D. Feil, D. G. Kubier, and D. J. Wells, Jr., J. Org. Chem. 40, 1478 (1975).
R. A. McClelland, J. Am. Chem. Soc. 97, 3177 (1975).
W. P. Jencks, Catalysis in Chemistry and Enzymology, McGraw-Hill Book Co., New York, 1969.
M. L. Bender, Mechanisms of Homogeneous Catalysis from Protons to Proteins, Wiley-Interscience, New York, 1971.
T. C. Bruice and S. J. Benkovic, Bioorganic Mechanisms, Benjamin, New York, 1966.
A. J. Kirby and A. R. Fersht, in Progress in Bioorganic Chemistry, Vol. 1, E. T. Kaiser and F. J. Kézdy (eds.), Wiley-Interscience, New York, 1971, pp. 1–82.
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Carey, F.A., Sundberg, R.J. (1977). Reactions of Carbonyl Compounds. In: Advanced Organic Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-8882-5_8
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DOI: https://doi.org/10.1007/978-1-4615-8882-5_8
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